5-Fluorobenzothiophene-2-boronic acid

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5-Fluorobenzothiophene-2-boronic acid Basic information
Product Name:5-Fluorobenzothiophene-2-boronic acid
Synonyms:5-Fluorobenzothiophene-2-boronic acid;5-FLUOROBENZO[B]THIEN-2-YL BORONIC ACID;5-fluorobenzo[b]thiophen-2-ylboronic acid;5-Fluorobenzo[b]thiophene-2-boronic acid;(5-fluoro-1-benzothiophen-2-yl)boronic acid;Boronic acid, (5-fluorobenzo[b]thien-2-yl)- (9CI);5-Fluorobenzo[b]thiene-2-boronic acid;CAS:501944-42-9
CAS:501944-42-9
MF:C8H6BFO2S
MW:196.01
EINECS:
Product Categories:
Mol File:501944-42-9.mol
5-Fluorobenzothiophene-2-boronic acid Structure
5-Fluorobenzothiophene-2-boronic acid Chemical Properties
Boiling point 393.2±45.0 °C(Predicted)
density 1.44±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
pka6.65±0.30(Predicted)
Safety Information
HS Code 2934999090
MSDS Information
5-Fluorobenzothiophene-2-boronic acid Usage And Synthesis
Synthesis
5-FLUOROBENZO[B]THIOPHENE

70060-12-7

Trimethyl borate

121-43-7

5-Fluorobenzothiophene-2-boronic acid

501944-42-9

General procedure for the synthesis of 5-fluorobenzothiophene-2-boronic acid from 5-fluorobenzothiophene and trimethyl borate: 5-fluorobenzothiophene (0.374 g, 2.5 mmol) was dissolved in anhydrous tetrahydrofuran (3.5 mL) in a three-necked flask under argon protection. n-Butyllithium (1.2 mL, 3 mmol) was slowly added at -78 °C to -68 °C and reacted for 25 min. Subsequently, trimethyl borate (0.33 mL, 3 mmol) was added dropwise and the reaction mixture was slowly brought to room temperature with continuous stirring for 3 hours. Upon completion of the reaction, the pH was adjusted to 6 by adding dilute hydrochloric acid and diluted with water (50 mL). Extracted with ethyl acetate (50 mL x 3), the organic phases were combined, washed once with saturated saline (50 mL) and dried over anhydrous sodium sulfate. Purified by silica gel column chromatography with dichloromethane:methanol=25:1 as eluent, a light yellow solid powder was obtained (target product 5-fluorobenzothiophene-2-boronic acid, 0.2 g, yield 38%).

References[1] Patent: CN105294785, 2016, A. Location in patent: Paragraph 0063; 0064
5-Fluorobenzothiophene-2-boronic acid Preparation Products And Raw materials
Raw materials5-Fluorobenzo[b]thiophene-->Trimethyl borate-->Tetrahydrofuran-->n-Butyllithium
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